(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester → 1-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 2363396Notes

Reaction equation

HRID 2363396 reaction equation
C(O[C:5](=[O:16])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13][CH2:14][CH3:15])C=C.C(OC([CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29](=[O:44])[CH:30]([NH:32][C:33](=[O:43])[C:34]1[CH:39]=[C:38]([Cl:40])[C:37]([NH2:41])=[C:36]([Cl:42])[CH:35]=1)[CH3:31])=O)(C)(C)C.O=C1OC(OCCC2C=CC=CC=2)C(NC(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)C1>>[CH2:14]([O:13][CH:8]1[CH:7]([NH:6][C:5]([CH:24]2[CH2:28][CH2:27][CH2:26][N:25]2[C:29](=[O:44])[CH:30]([NH:32][C:33](=[O:43])[C:34]2[CH:39]=[C:38]([Cl:40])[C:37]([NH2:41])=[C:36]([Cl:42])[CH:35]=2)[CH3:31])=[O:16])[CH2:11][C:10](=[O:12])[O:9]1)[CH3:15]

Participants

4

Reactant 3

HCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 689509841-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 229774911-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 54%

Procedure

Prepared from (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 1-[2-(4-amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester according to the method used for 98a to afford 158 mg of title compound (54% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.08-1.30 (m, 3H), 1.32-1.52 (m, 3H), 1.72-2.44 (m, 4H), 2.40-3.05 (m, 2H), 3.50-3.97 (m, 4H), 4.25-4.70 (m, 3H), 4.70-4.86 (m, 1H), 5.33 (s, 0.4H), 5.47 (s, 0.1H), 5.56 (d, 0.4H), 5.62 (d, 0.1H), 7.50 (s, 1H), 7.80 (s, 1H). Analytical HPLC: 10.84 min. LC-MS (ES+): m/e=501.2 (M+H+).

Sources & evidence

ORD record
ord-be1e78bcb58b4876a5ed870bb6c4829e
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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